Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1984-04-23
1986-08-12
Shippen, Michael L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
549369, 549374, 549420, 549453, 549455, 556118, 556436, 560 8, 560 20, 560 21, 560 51, 560 52, 560 55, 560 56, 560 57, 560100, 560102, 560105, 562405, 562434, 562419, 562435, 562459, 562462, 562465, 562466, 562460, 568323, 568328, 562490, 568335, 568336, 562492, 568337, 568425, 562496, 568426, 568592, 568309, 558 51, 568319, C07C 5116
Patent
active
046057587
ABSTRACT:
Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.
REFERENCES:
patent: 2397412 (1946-03-01), Emerson
patent: 2444400 (1948-06-01), Emerson
patent: 2824139 (1978-02-01), Barnhart
patent: 2873275 (1959-02-01), Ramsden
Kharasch, "Grignard Reactions of Nonmetallic Substances," pp. 709-766, 846-851 and 870-879 (1954).
Cason, J. Am. Chem. Soc., 68, p. 2076 (1946).
Milsow, J. Am. Chem. Soc., 75, pp. 2318-2322 (1953).
Seebach, Angew. Chem. Internat. Ed., 7, pp. 619-621 (1968).
Dhuey John A.
Shippen Michael L.
Syntex Pharmaceuticals International Ltd.
LandOfFree
Preparation of .alpha.-arylalkanoic acids does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Preparation of .alpha.-arylalkanoic acids, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of .alpha.-arylalkanoic acids will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1945807